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Access to polyhydroxylated cycloheptane derivatives through stereoselective nitrile oxide intramolecular cycloaddition. Synthesis of an analogue of calystegine B2

✍ Scribed by O Duclos; A Duréault; J.C Depezay

Publisher: Elsevier Science
Year: 1992
Tongue: French
Weight: 240 KB
Volume: 33
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)91860-4

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✦ Synopsis

A hydroxymethyl substituted calystegine B2 has been synthesized stereoselectively by intramolecular cycloaddition of an olefinic nitrile oxide derived from D-glucose. Calystegines B 1, B2, A3 are new alkaloids of the tropane family, isolated from the roots of calystegia .s~p~um : they might act as nutritional mediators of specific plant-bacterium relationshipsl. 01 R=H 4 A3 R=CH20H 10 Chemical syntheses of the enantiomerically pure calystegines and of analogues are useful for biological tests' and also to confirm the recently spectroscopically established structure of calysteginesz.

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